Triethylamine → 3-Methoxypyridine-2-carbonitrile

3-Methoxypyridine-1-oxide (25.2 g, 209 mmol) was dissolved in acetonitrile (260 mL). Trimethylsilycyanide (66.35 g, 669 mmol) and triethylamine (45.13 g, 446 mmol) were added and the reaction mixture heated at reflux for overnight. The cooled solution was concentrated in vacuo to give a brown solid which was partitioned between CH2Cl2 and 3M Na2CO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chomatography using 1:1 EtOAc/hexanes as eluent. Compound 762B was isolated (17.63 g, 63%) as a light yellow solid. HPLC: 96.2% at 1.37 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 134.88 [M+H]+.

1. temperaturethe reaction mixture heated
2. temperatureat reflux for overnight
3. concentrationThe cooled solution was concentrated in vacuo
4. customto give a brown solid which
5. customwas partitioned between CH2Cl2 and 3M Na2CO3
6. customThe organic layer was separated
7. washwashed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica gel chomatography

ORD record

ord-f7b22a35d75744599c5585868efbbba6

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517904B2